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Job Description
About us: At Two Pines, we're more than just a vacation rental company, we're a close-knit team of passionate professionals dedicated to delivering exceptional experiences to our guests and homeowners. As the largest locally owned and operated vacation rental company in Big Sky, we pride ourselves on creating meaningful impact within our community, and we're looking for like-minded individuals to join our team. We offer a dynamic, fun, and supportive work environment where you'll not only contribute to our company's growth but also thrive in a place that offers an unparalleled work-life balance. Whether it's skiing powder in the winter, hiking world-class trails in the summer, or building lasting relationships with guests, homeowners, and teammates, working at Two Pines means living and working in one of the most exciting resort towns in the country.
Position Overview:
The Property Manager is responsible for the day-to-day management of a portfolio of high-end vacation rental homes. You'll ensure properties are well-maintained, guest-ready, and meeting Two Pines' elevated standards through proactive inspections, coordinated workflows, and exceptional service to both guests and homeowners. This role requires strong organization, clear communication, and the ability to problem-solve in a fast-paced, guest-focused environment. You will collaborate closely with maintenance technicians, Property Inspectors, vendors, and our guest services team to keep operations smooth, especially during peak ski and summer seasons. Key Responsibilities Property Care & Operations Conduct regular property check-ins to verify quality standards and guest readiness. Perform, schedule, coordinate, and oversee maintenance work, repairs, and routine services. Communicate with vendors and contractors to ensure timely, high-quality work. Complete inspections prior to homeowner-specific arrivals. Assist with minor hands-on property care as needed, such as assembling small furniture, lifting and carrying up to 50 lbs, light painting, basic repairs, replacing light bulbs, removing trash, and coordinating larger maintenance items with vendors or the Maintenance team. Homeowner Relations Build and strengthen trust-based relationships with property owners through proactive communication. Provide updates on property condition, maintenance needs, and overall property health. Address owner questions and concerns with professionalism, accuracy, and transparency. Utilize email and company-provided software to track tasks, document property status, and maintain clear communication with owners, vendors, and staff. Preferred Skills Basic knowledge of home maintenance, common repairs, and property operations. Familiarity with Big Sky, local vendors, and seasonal home needs preferred, but not required. Willingness to learn local property requirements, weather-related challenges, and company standards. Strong computer and technology skills, including using apps, property management software, and communication tools. Ability to work independently, manage time effectively, and problem-solve without constant supervision. Current Montana Property Manager License preferred, but not required. Prior experience in property management, vacation rentals, hospitality operations, or owner relations preferred.
Compensation:
Starting wage of $27-$30 per hour, based on experience, with approximately 40 hours per week. Performance reviews will occur after the initial 60-day period, followed by annual reviews. Merit-based increases may be awarded based on performance.
Benefits:
Health insurance options with employer contributions Dental and vision insurance 401(k) eligibility after six months of employment with company match PTO Big Sky Resort ski pass available for eligible employees
Employee Housing:
We offer affordable employee housing in well-maintained homes, townhouses, and condos. Each employee has their own private bedroom while sharing common spaces such as the kitchen and bathroom with fellow team members. Monthly rates are affordable, and availability details can be provided upon request.
Conditions of Employment:
Must pass a background check and motor vehicle record check. Must have a clean driving record for at least 3 years and maintain it during employment. Must sign required employment and confidentiality agreements. Must be able to work weekends and holidays as needed.
Job Details Job Type:
Full-time, year-round
Work Location:
Must be located in or able to relocate to Big Sky, MT before starting.
Job Type:
Full-time Pay:
$27.00 - $30.00 per hour
Benefits:
401(k) 401(k) matching Dental insurance Health insurance Paid time off Vision insurance Application Question(s): Are you currently located in Big Sky, MT or able to relocate to Big Sky before starting work? If relocation is needed, please provide your expected relocation timeline. Do you have a valid driver's license and a clean driving record for at least the last 3 years? Are you willing and able to complete a background check, motor vehicle record check, and sign required employment/confidentiality agreements, including a non-disclosure agreement? Please briefly describe your experience in property management, vacation rentals, hospitality operations, owner/client relations, maintenance coordination, or a related field. Two Pines is a close-knit, service-focused team that values high standards, accountability, flexibility, and clear communication. Why do you feel you would be a strong fit for our team? Are you comfortable completing minor hands-on property care tasks as needed, such as assembling small furniture, lifting/carrying up to 50 lbs, light painting, basic repairs, replacing light bulbs, removing trash, and coordinating larger maintenance items with vendors or our maintenance team?
